When comparing OpenSSH vs WinSCP, the Slant community recommends OpenSSH for most people. In the question“What are the best SSH clients for Windows?” OpenSSH is ranked 2nd while WinSCP is ranked 17th. The most important reason people chose OpenSSH is:
If you find samples or tutorials about SSH, they almost always refer to OpenSSH. It bascially defines what SSH is.
Specs
Ranked in these QuestionsQuestion Ranking
Pros
Pro The Reference SSH Client
If you find samples or tutorials about SSH, they almost always refer to OpenSSH. It bascially defines what SSH is.
Pro One of the most trustworthy development teams on the web
The development team of OpenSSH is part of the OpenBSD ecosystem. Their implementation is basically today's technical reference for any SSH client.
Pro Available on virtually any platform
MacOS. Windows. Core component on any Linux flavor.
Pro Standard implementation that documentation for all other tools assumes you have installed already
A lot of other tools (e.g. git) are based on this for file transfer.
Pro Supports FTP and SFTP
In new versions also supports WebDav.
Pro Free and open-source
It has very good compatibility with the other tools of this segment (e.g. PuTTY).
Pro Supports WebDAV
Pro Not bundled with Potentially Unwanted Programs (PUP)
Does not attempt to install unwanted software on installation.
Pro Supports PPK Keys
You can use the SSH server public/private key files from putty to log in.
Pro Supports Amazon S3
You can use in the last versions S3 so you're good if you use Amazon AWS.
Pro Portable
No Installation required.
Pro Integrated basic text editor
It has a integrated basic function text editor to create/edit/update files directly from client.
Pro Can protect stored passwords by strong AES cipher
Pro Can be automated with batch scripts
Put a line in bat file ""D:\Program Files\WinSCP\winscp.com" /console /script="D:\ftp\scripts\transfer.txt". All the info can be found on their site.
Cons
Con No host list
Has no functions to manage huge numbers of hosts.
Con No way to organize SSH connections
No way to organize SSH connections.
Con Command line tool
It can be difficult to use from a command line interface.
Con Keyboard shortcuts not editable
Con Slow
In my opinion, it's slower than Filezilla.
Con No x64 version
Con Does not support UNC
Does not support UNC. This makes working with the "Library"-function in Win 7, 8, 10 not possible when working over a network.
Con Weird keyboard selection handling
If you are accustomed to several commanders, the selection method in WinSCP behaves unexpected - most often selects too much.